Over the years, this building has housed several businesses including "furnishing goods," a tailor shop, a piano store, a jewelry store, a bank, and an abstract office.

In 1864, the post office was in a wooden structure on this lot.

For many years in the late 1800's, The Winterset Madisonian newspaper office was on the second floor. Access to the second floor was gained from an outside stairway on the south side of the building. The stairway differed from most outside stairways in that it rose from both the front and the back of the building to a landing at the outside door on the second floor. In 1896 a gasoline engine powering the printing press exploded and caused a fire.

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